Our team is dedicated to finding and telling you more about the web’s best products. If you purchase through our links, we may receive a commission. Our editorial team is independent and only endorses products we believe in.
I consider myself something of a boot expert: where some girls keep a Carrie Bradshaw-esque collection of skimpy sandals, I’ve carved out a dedicated boot closet in my tiny New York apartment. The second spring gives way to summer and I have to retire my rainboots, I start dreaming about boot-centric autumnal outfits. Even when I lived in balmy LA, I pounced on any opportunity to break out a minidress-and-knee-high combo. This minor obsession means that my eyes remain glued to the footwear during fashion week. And after years of relatively straightforward trends, I’m delighted to report that change is in the air.
If the F/W 26 runway shows are any indicator, this fall is shaping up to be dominated by a single ethos in the footwear department: from chunky Chelseas to witchy lace-ups, boots are taking a turn for the freaky this fall. We’ve already seen this trend elsewhere – think puffed up sneakers and sandals from a couple years ago or last year’s “freaky little shoe” trend, coined by trend forecaster Mandy Lee – but it’s taken a while to trickle down into full-fledged boots. In my boot trend guide below, I’ve included the luxury brand blueprints for inspo (and those who want to really invest in a signature pair), along with covetable, well-made mid-priced dupes.
As an avid boot collector, I’m extremely excited to dive into the freakiest fringes of the deep end. But for those who merely want to dip a toe, I’ve organized this guide to fall boot trends from least freaky to freakiest. Embrace the freaky boot on your own terms this fall, whether that’s adding an outsized sole to your classic Chelsea boot, or giving a bold animal print a spin.
Read on for our essential guide to 2026’s runway-inspired freaky boot trend:
We like
We don't like
The Chunky Chelsea
Let’s start off with an update on a familiar silhouette. You know her, you love her: the black Chelsea boot. Classic, dependable, and dying for a little twist to make her relevant again. The easiest way to make an ankle boot feel very 2026 is by adding a freaky, chunky sole. The blueprint for this trend is the Prada Monolith Chelsea Boot ($1650), which I have a feeling will be everywhere this fall. For a chunky sole, I’d go straight to the source: Camper. The Spanish footwear brand has been pioneering freaky footwear for decades. You could take things in a sleek, mod direction with the Camper Milah in Black ($250). Or go even bolder with the hyper-textured sole of the Camper Pix London in Black ($250).
Zip Me Up
If you’re feeling more inspired by The Row Zipped Ankle Boot ($1490), add a zip to your chunky ankle boot. I love the sleek ME+EM Zip Front Boot ($675). The Staud Miles Zip Ankle Boot in Black ($495) adds another subtle freaky layer with the textured lug sole. Or add a little freaky flair with the Swedish Hasbeens Bootcut Boot in Black ($275), which features a back zip.
Witchy Lace Ups
There’s something deliciously witchy (and autumnally-appropriate) about lace up boots to me – maybe we can blame The Wizard Of Oz. The Row Kai Lace Up Boot ($1750) is the perfect combo of timeless and on-trend. The Christy Dawn The Dawn Boot in Black ($358) would be perfect peeking out from a maxi skirt. The Aeyde Isa Lace-Up Ankle Boots ($845) make a great investment piece, and have the added bonus of zips (no tying and untying needed). I’m a sucker for a good knee high, and my favorite boot in this entire guide is the side-laced Anonymous Copenhagen Dico Ann Side Laces Boots in Coffee Brown ($505).
Animal Print Antics
I think my favorite freaky boot trend of the year is the return of animal print. In my opinion, the Marni White And Brown Cow-Print Ponyhair Boot ($1695) is the north star for this trend. The Rouje DORIA Ankle Boot ($445) and Aquaitalia Siella 45mm Leopard-Print Calfhair Ankle Boot ($475) have a similar bold print and low heel. And I love how the Freda Salvador Jolene Western Ankle Boot in Cow Haircalf ($550) offers a spin on the trendy Western silhouette.
Sky High Thigh Highs
Chloé, Hermes, Balenciaga, and more all featured thigh highs in their womenswear F/W 26 shows, and Saint Laurent even wove the trend into their menswear collection. My personal favorites were the burgundy Dries Van Noten Leather Over-The-Knee Boots ($1925). I love the decadent wine red and ultra slim heel of the Ulla Johnson Carolina Slouchy 55mm Over-The-Knee Suede Boots in Cognac ($410). The Staud Wally 55mm Over-The-Knee Boots in Black ($298) definitely channel Andie’s Chanel thigh-highs in The Devil Wears Prada. And the Paris Texas Bettina Over The Knee Boot 50 ($625) adds a chic western silhouette to the over the knee trend.
Whether you’re just adding an unexpected accent to a familiar silhouette, or are ready to fully commit to making an entrance in over-the-knee conversation starters, freaky boots are fall’s biggest footwear trend. Shop our runway-inspired guide to get the look.
